Anthracene dye.



' To all whowi it may concern:

9 lie, residing at Mannheim, Germany, have I a specification;

- UNITED STATES ivmx stream xunz t inem-Em, Guam N sons FABRIK, 011E,LUIPYTIQSHAFEN:ON-llHE-QRHIIITE, (mann ng;- oonrona 'r on Q I i H ANrHnAcnN1i DYE. I Y I i I i I No Drawing.

Be it knownthat-I, MAX ALBERT Km, Ph, D. ,:chemifst,' citizen of the Swiss Repubinvented new andfuseful Improvements in A nthracene Dyes, ofwhich the following is.

.' My lnvention relates to new coloring inatters of the anthracene methyl derivatives ,of N-dihydro-anthi-aquinon-azin (indanthrene blue) containing one or more methyl groups attached to carbon atoms of the, anthracene residues.

y new Jcoloring matters can be produced by applying any of the methods which are employed for the production of indanthrene blue itself to the corresponding methylated.

initial materials, namely by melting 2-aminomethyl-anthraquinon with caustic potash and oxidizing the leuco compound thus formed .(cf. Patent No. 682,523), or by treating Q-iamino-methyl-anthraquinon with an oxidizing agent (cf. Patent No.- 7 39,145), or by treating 1amino-Inethyl-anthraquinon with an acid agent or a metallic salt: (cf. Patent No. 855,248). Other methods of producing indanthrene blue or halogenated products thereof consist treating Lamino-2 halo gen-anthraquinon or 2sainino-L3-dihalogenanthraquinon with a suitable condensation agent (of. British Patent No. 7 692/01) and in condensing an ortho-diamino-anthraquinon with an ortho-dihydroxy-anthraquinon (of. British Patent No. 9102/06), and these processes can also be applied to methyl-sub;

stituted initial materials.

' My said new coloring matters possess, all.

the valuable properties of the indanthrene coloring matters and further difier in some respects from the indanthrene blues, so

that they afl'ord a, valuable addition to this group ofproducts. Thus for instance the 33 dimethyl inda'nt-hrene from 2-amino-3-methyl-anthraquinon possesses a much greener shade of blue than does indanthrene blue-itself, obtained from 2-aminoanthraquinon. On the otherhand, the dimethyl-indanthreneobtained from 6- methyl 2 amino anthraquinon possesses shades which are similar'to those 'indanthreneblue-itself, but it diifers from it in other ways.. All my new color-ingmat ters are characterized by being more soluble in nitrobenzene than in indan-threne blue- Specification of Letters Patent. Application filed January 31, 1911. Seriallio. 8053178322" well I as the-gmethyl series which are jtheanthraquinon nitrogen atom-of the aminogroup, or both Example 1 Boil together, for

obtained ielded by 4 assreno'n TO I rams can ANILIN .i anted-my 1e,-1e1

itself, and they also have excellent dyeing properties and are veryfast. I i' K If desired, in producin the new'coloring matters of my invention; erivatives of amino-anthraquinon can contain another group, "or other 'groups,.jas oup, thesaidpther group, orgroups, being situated either in residue, or attached to the being situated in the said. oup and atta'ched to the said, atom. Similar: coloring matters-can also beobtained by condensing an"oitho-diamino anthraquinon with orthodihydroxy-methyl-anthraquinoni' j The following exampleslillustrate methods of producing some of my new coloring mat-' ters, but I do not limitmy invention to the coloring matters therein described. The parts are by'weight. Y

gne art of; 2.3-amino-inethy -anthraquinon, orty parts of glacial acetic acid, and three parts of lead roxid -.'f When the mix- 'tureis cold, filter o bo l it with dilute move" the lead. threne blue thus obtained 'canbe crystallized froma large quantity .of nitrobenzene and obtained in the hydrochloric acid to recultly soluble in organic solvents and yields, a blue vat which colors'cotton blue shades I which, upon washing; are ,converted into bluish green shades. In a similar Iinanner, coloring matters can be ob; ainedffrom :6- methyl-2-amino-anthraquinon and" i methyl-2-amino-anthraquinon.

the coloring matter and The 3.3-'dimethyl-indan- I pureform. It is a 'bluish green crystalline powder-which is verydiflibe employed which three hours,

Example 2-: Introduce one part of 7 a methyl-2-amino-anthraquinon into four parts of caustic potash at a, temperature offromv two" hundred to two hundred and fifty de grees centigrade, and then (while stirring) continue heating for thirty minutes at the same temperature. When the melt is cold, boil it with water, and filter and wash. The

7 .7 -dimethyl-indanthreneblue can be crystallized from nitrobenzene and. obtained as a dark bluecrystalline powder, It yieldaa.

blue vat which dyes cotton dark blue shades, and has great covering power. In a similar-manner, 6.6-dimethyl-indanthrene blue can be. obtained from .6-methyl-2-aminoanthraquinoni kalis, but are Examp e 3: Boil together, for from four to five hours, ten parts ofl-bromQ-amino- 3-methyhanthraquinon, one hundred. and twenty parts of naphthalene, one part of copper oxid, five parts of anhydrous sodium acetate, and four parts of inagnesium oxid. While'the mass is hot, filter off the bluish green coloring matter and wash it, su'cces: sively, with hot alcohol, dilute hydrochloric acid, and water; that obtained according to the foregoing first example.

1., The new-*"coloring matters-of the ans thracene Qseries being methyhindanthrene blues containing at least one methyl group attachedt'o acarbon atom of the anthracene residue, which new coloring matters are insoluble in water and in-dilute acids and alyielding vats to carbon atoms of the anthracene residue The product is similar to soluble in alkalinehydrosulfite which dye cotton from blue to 3 green shades, and which coloring matters are condition show a composition corresponding to the formula G l-1 N 0 and are insoluble in water and in.dilute acids and alkalis, but

are soluble in alkaline hydrosulfite yieldingv yat's which dye cotton from blue to green shades, and which coloring matters are more soluble in nitrobenzene than is ordinary nonmethylated indanthrene' blue.

3. The new C lOI'IIIg matter being 3.3- dimethyl-indanthrene blue which consists when dry of a bluish green powder which yields a blue vat which colors cotton blue shades which upon washing are converted into bluish green shades, and which coloring matter is insoluble in water and .in dilute acids and alkalis-and is diflicultly soluble in most organic solvents, but is more soluble in 'nitrobenzene' than is ordinary indan threne blue.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing witnesses.

c MAX, ALBERTKUNZ.

Witnesses: I

J. ALno. LLOYD, A. O. TITIMANN.

or residues, which upon analysis in the pure- I 

